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Best Buy Theatre was dense with sneakers and snapbacks on Monday night for the Monster Energy Outbreak tour featuring XXL Freshman Class 2012, starring the ten buzzing MCs that graced the hip-hop magazine's annual "Freshman" cover. Hosted by Hot 97 personalities Cipha Sounds and Peter Rosenberg, the concert aimed to showcase the best among today's emerging hip-hop acts – the promising artists set to graduate into tomorrow's superstars. But the disjointed, unrealized and at times laborious performances suggested that this class wasn't quite prepared for the first day of school.

After routine opening sets from Don Trip and Kid Ink, recent Interscope signee Iggy Azalea pranced onstage with the aid of an enthusiastic hypeman, who did much of the heavy lifting. The polarizing Australian rapper barely spoke, but her quasi-trademark sways and dips translated accurately from YouTube to stage as she rambled through cuts from her Ignorant Art mixtape. "Are my Azaliens in the motherfucking building?" her sidekick shouted, to little response. A visibly nervous Iggy did little to win over new fans, fumbling her lyrics at least twice. After performing her latest T.I. collaboration, "Murda Bizness" ("It's not on the radio yet!" she briefed), Iggy hopped into the crowd to give hugs to attendees as her hypeman interpolated Tupac: "All eyez on Iggy!" he chanted. Too early, perhaps.

The rest of the evening highlighted much of the same tension between the sinister irony of the web and the raw scrutiny of the stage. From the triple-distilled Slim Shady bites of Hopsin, to the piercing delivery and sneering humor of Danny Brown (who was promptly booed), the bill offered up a spread of artists that have found clusters of relevance within the vastness of the post-Napster listening audience, but none who demand standing ovations. Each performer claimed at least a dozen or so diehards whose cheers and chants distracted from the blank stares of remaining onlookers. Still, budding hook-men Roscoe Dash and Future swayed fans with the aid of some radio-heavy collaborations, and French Montana's slow burning street anthem "Shot Caller" clapped with authority throughout the New York audience – his special guest DJ Khaled brought the night its mainstream peak and was a welcome familiar face after nearly three hours of fringe.

The most fully realized performer was Cleveland's Machine Gun Kelly, whose pack of devotees had been chanting his initials all night. Accompanied by a DJ and drummer, the Bad Boy-signee ran through his rage-rap anthem "Wild Boy" and the shot-chasing "LTFU," which blends Daft Punk with Pimp C. He littered his sentences with profanity (To his fans: "You motherfuckers make my day better, motherfuckers") and at one point stripped to his boxer-briefs to mime Blink 182's "What's My Age Again?" Truthfully, Kelly's punk-hop shares more DNA with Travis Barker than Waka Flocka; worlds collided with a wet crash as the mohawked MC slammed his head against a cymbal to close his set. "I was never supposed to be on this stage," he panted, shirtless and soaked. But somehow, at a rap concert sponsored by a rap magazine and hosted by rap DJs, his performance made the most sense of the night.